HCID 57839057, compound → HCID 57839056, compound

HRID 732951Notes

Reaction equation

HRID 732951 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:10]1>C1(C)C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[N:12]=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:10]=1.[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:19])[N:12]=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:10]=1

Participants

5

Reactant 1

HCID 57839057HCID 57839057, compound

Product 2

HCID 57839056HCID 57839056, compoundYield 23%HCID 69052353HCID 69052353, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of methyl 4-(2,4-dichlorophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate (600 mg, 1.76 mmol) in PhCH3 (6 mL) was added MnO2 (227 mg, 2.64 mmol) and the reaction was heated to 95° C. for 14 hrs. The reaction was filtered through a pad of celite, concentrated under reduced pressure, and purified by flash chromatography (silica gel, 30% EtOAc/hexane) to give methyl 4-(2,4-dichlorophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate (150 mg, 23% for 2 steps) and 4-(2,4-dichlorophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylic acid (100 mg, 15% for 2 steps).

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationconcentrated under reduced pressure
  3. custompurified by flash chromatography (silica gel, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-c575733811d545d6992d5b72ce3c1263
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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